HCID 67170252, compound → HCID 67169865, compound

HRID 1475713Notes

Reaction equation

HRID 1475713 reaction equation
C([O:8][CH:9]1[CH2:13][CH2:12][CH2:11][C:10]1([NH:17][C:18](=[O:37])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH2:28][CH2:29][C:30]2[CH:31]=[C:32]([CH3:36])[CH:33]=[CH:34][CH:35]=2)[CH:20]=1)[C:14]([OH:16])=[O:15])C1C=CC=CC=1>C(O)C.[Pd].[H][H]>[OH:8][CH:9]1[CH2:13][CH2:12][CH2:11][C:10]1([NH:17][C:18](=[O:37])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH2:28][CH2:29][C:30]2[CH:31]=[C:32]([CH3:36])[CH:33]=[CH:34][CH:35]=2)[CH:20]=1)[C:14]([OH:16])=[O:15]

Participants

5

Reactant 1

HCID 67170252HCID 67170252, compound

Product 1

HCID 67169865HCID 67169865, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 23938PalladiumSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

Diastereomer 1 and diastereomer 2 of the compound of example 66 were separately dissolved in ethanol and hydrogenated with palladium 10% on charcoal at room temperature with 1 bar hydrogen pressure until completion of the reaction. After filtration, the solutions were evaporated to dryness and the residues purified by RP HPLC (water/ACN gradient) to yield the two diastereomers of the title compound separately.

Workup

  1. filtrationAfter filtration
  2. customthe solutions were evaporated to dryness
  3. customthe residues purified by RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-1d483ea5ed984b51b7ed0e910cf56fef
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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